34371-14-7Relevant articles and documents
Isolation and characterization of two furan-side photoadducts of 7-methylpyrido[3,4-c] psoralen to the sugar moiety of 2′-deoxyadenosine
Voituriez, Lucienne,Cadet, Jean
, p. 152 - 158 (1999)
The UVA-mediated photoreaction of the monofunctional 7-methylpyrido[3,4-c]psoralen (MePyPs) with 2′-deoxyadenosine was investigated in the dry state. Two main 7-methylpyrido[3,4-c]psoralen monoadducts to 2′-deoxyadenosine were isolated by HPLC and characterized by soft ionization mass spectrometry (fast atom bombardment) and extensive 1H NMR analyses including correlation spectroscopy, total correlation spectroscopy and nuclear Overhauser effect measurements. The two unusual photoadducts exhibit a covalent bond between the C-4′ of the furan moiety of the psoralen on one hand and either the C-1′ or the C-4′ of the furanose ring of the purine nucleoside on the other hand. The furan-side monoadducts appear to be specific for both 2′-deoxyadenosine and MePyPs. They are likely to result from the recombination of the 4′,5′-dihydrofuran-4′-yl radical of MePyPs with 2′-deoxyadenosyl carbon-centered sugar radicals at either the 1′ or the 5′ position.
Towards a DNA-like duplex without hydrogen bonds
Mathis, Gerald,Schuetz, Rolf,Hunziker, Juerg
, p. 1183 - 1185 (2003)
The inverse quadrupolar moments of the phenyl and pentafluorophenyl residues in the base pair P-F5 promotes strong intramolecular stacking interactions in DNA duplexes. The more natural base pairs are replaced by this novel pair the higher the thermodynamic stability of the resulting duplex if they are arranged in an alternating fashion.
Lanthanide(III) Catalyzed Aldol Reactions of Glyceraldehyde Acetonide with Ketene Silyl Acetals: Catalytic Asymmetric Route to Monosaccharides
Mikami, Koichi,Terada, Masahiro,Nakai, Takeshi
, p. 993 - 996 (1991)
The Pr-, Eu- and Ho(dppm)3 catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals are described, where remarkably high anti-diastereofacial selection is achieved.Thus, the asymmetric synthesis of 2-deoxy-D-ribonolactone and formal synthesis of 2-amino-2-deoxy-D-pentose by the lanthanide(III) catalyzed aldol reaction with ketene silyl acetals of acetate and α-chloroacetate, respectively are described.
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Cadet,Teoule
, p. 3225,3228 (1972)
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Stereospecific 1,2-hydride shift in ribonolactone formation in the photoreaction of 2′-iododeoxyuridine
Sugiyama, Hiroshi,Fujimoto, Kenzo,Saito, Isao
, p. 2945 - 2946 (1995)
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Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates
Song, Jie,Hollingsworth, Rawle I.
, p. 387 - 391 (2001)
Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-δ-lactone and L-mannonic acid-γ-lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1,3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone.
CYCLOPENTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS
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Paragraph 0300, (2020/07/07)
Described herein are cyclopentyl nucleoside analogs, pharmaceutical compositions that include one or more cyclopentyl nucleoside analogs and methods of using the same to treat HBV, HDV and/or HIV.
Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis-a novel transformation in carbohydrate chemistry
Draskovits, Markus,Kalaus, Hubert,Stanetty, Christian,Mihovilovic, Marko D.
, p. 12144 - 12147 (2019/10/21)
The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst design allowed the tuning of the selectivity of the reaction with structurally unbiased starting materials towards either of the two scenarios.
